US20040171896A1 - Preparation of compounds with the CF3 group - Google Patents
Preparation of compounds with the CF3 group Download PDFInfo
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- US20040171896A1 US20040171896A1 US10/790,686 US79068604A US2004171896A1 US 20040171896 A1 US20040171896 A1 US 20040171896A1 US 79068604 A US79068604 A US 79068604A US 2004171896 A1 US2004171896 A1 US 2004171896A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 41
- YMRMDGSNYHCUCL-UHFFFAOYSA-N 1,2-dichloro-1,1,2-trifluoroethane Chemical compound FC(Cl)C(F)(F)Cl YMRMDGSNYHCUCL-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 halocarbon compounds Chemical class 0.000 claims abstract description 5
- 150000001463 antimony compounds Chemical class 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 238000005260 corrosion Methods 0.000 claims description 4
- 230000007797 corrosion Effects 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- AFTSHZRGGNMLHC-UHFFFAOYSA-N 1,1-dichloro-1,2,2-trifluoroethane Chemical compound FC(F)C(F)(Cl)Cl AFTSHZRGGNMLHC-UHFFFAOYSA-N 0.000 claims 1
- 238000006317 isomerization reaction Methods 0.000 abstract description 11
- 239000003054 catalyst Substances 0.000 abstract description 6
- 150000008282 halocarbons Chemical class 0.000 abstract description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 1
- 150000001462 antimony Chemical class 0.000 abstract 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 9
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 239000004604 Blowing Agent Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/395—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification of at least one compound
Definitions
- the invention relates to a method for the preparation of compounds with a CF 3 group by making use of isomerization.
- Halogenated hydrocarbon compounds can be used, for example, as refrigerants, blowing agents and also as intermediates in chemical syntheses.
- the compound CF 3 CHCl 2 for example, is used as a component of refrigerants and blowing agents. It can also be converted by photooxidation into trifluoroacetyl chloride.
- Another object of the invention is to provide a new method for the preparation of compounds which contain the CF 3 group, in which the method is carried out via an isomerization reaction.
- An additional object of the invention is to provide a method for purifying compounds which contain the CF 3 group which are contaminated by isomeric contaminants.
- X represents H, Cl or F and Y represents H, Cl, F, C1-C3 alkyl, or C1-C3 alkyl substituted by at least one halogen atom, with the proviso that X and Y cannot simultaneously represent fluorine,
- X and Y have the meanings given above, are contacted with the antimony compound SbCl 0-0.5 F 4.5-5 .
- HF is also present at the same time. If, in this case, the sum of the HF and the antimony compound in the reaction mixture is 100 parts by weight, the HF is contained in an amount of 1 to 70 parts by weight and preferably of 20 to 50 parts by weight, the remainder up to 100 parts by weight being the antimony compound. If, in accordance with a preferred embodiment, HF is present, it may be assumed that the antimony compounds will be present in the form of HF adducts. In this case, contacting is carried out in the presence of HF adducts of SbCl 0-0.5 F 4-4.5 . A portion of not more than 10 mole percent of the antimony compound can also be replaced by Sb(III), for example, by SbF 3 .
- the contacting is carried out with antimony pentafluoride (in this connection, it should be kept in mind that, in the presence of HF, adducts of the antimony(V) compound are present, as mentioned above).
- Antimony pentafluoride is a commercially available product.
- the isomerization is carried out at a temperature ranging from 20° to 150° C., and preferably from 50° to 120° C.
- the pressure depends on the composition of the mixture and advantageously ranges from atmospheric pressure to 6 bar.
- the temperature and pressure are selected, in particular, so that the contacting is carried out in the liquid phase.
- the molar ratio of the compound of formula (II), the compound of formula (III), or the sum of the two compounds when both are present, to the antimony compound preferably ranges from 0.1:1 to 10:1, and particularly preferably from 0.5:1 to 2:1.
- the isomerization is carried out in a corrosion-resistant apparatus.
- Reactors and equipment parts which consist of aluminum or polytetrafluoroethylene (TeflonTM) or are coated with aluminum or polytetrafluoroethylene (TeflonTM) have proven to be particularly corrosion-resistant.
- a pre-fluorination with HF or F 2 carried out before the start of the reaction has been shown to have a positive effect on the corrosion behavior.
- the method of the invention can be carried out batchwise or continuously.
- the reaction can be conducted continuously in a bubble reactor, whereby the educt, or if HF is used at the same time, a mixture of HF and educt, is passed into the liquid antimony compound, and a mixture of product and HF is discharged.
- the product mixture is an azeotrope with HF, which, upon cooling, separates in the liquid phase into two phases.
- Sb(V) halide decomposes with formation of Sb(III) halide and halogen. If desired, Sb (II) halide can be converted once again into Sb(V) halide with chlorine or fluorine. This can be done batchwise or continuously, for example, with constant removal of a portion of the reaction mixture and treatment of the latter with halogen.
- the invention thus provides a novel method of effecting isomerization.
- the palette of usable isomerization catalysts is accordingly expanded.
- a mixture of 89.9% of 123, 10.0% of 123a and 0.1% of 123b was added to an autoclave with a TeflonTM liner and mixed in a ratio of 1:2 with the catalyst mixture.
- the composition of the catalyst was as follows:
- the autoclave was closed, heated to 110° C. and maintained at this temperature for one hour at a pressure of about five bar. It is assumed that an HF adduct of antimony pantafluoride was present in the reactor. Subsequently the autoclave was cooled with ice, and the pressure in the gas phase was relieved. The contents of the autoclave were hydrolyzed in ice/tartaric acid (tartaric acid because of the solubility of the Sb complex) (closed system) and the organic phase was separated from the aqueous phase. The purity of the 123 isomer isolated was 99.9%; in addition, 0.14% of newly formed 1,1,2-trifluoro-1,2,2-trichloroethane (113) were present. An additional Sb′′′ content of 1% was detected by the analysis of the aqueous phase treated with tartaric acid.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Highly fluorinated antimony, especially in the form of a hydrogen fluoride addition compound, can be used as an isomerization catalyst for the isomerization of certain halocarbon compounds or halogenated hydrocarbon compounds. For example, 1,1,1-trifluoro-2,2-dichoroethane can be produced from 1,1,2-trifluoro-1,2-dichloroethane. The method also is suitable for the purification of certain halocarbon or halogenated hydrocarbon compounds which are contaminated by isomerizable compounds.
Description
- This application is a continuation of international patent application no. PCT/EP02/09547, filed Aug. 27, 2002 designating the United States of America and published in German as WO 03/020675, the entire disclosure of which is incorporated herein by reference. Priority is claimed based on Federal Republic of Germany patent application no. DE 101 43 177.5, filed Sep. 4, 2001.
- The invention relates to a method for the preparation of compounds with a CF 3 group by making use of isomerization.
- Halogenated hydrocarbon compounds can be used, for example, as refrigerants, blowing agents and also as intermediates in chemical syntheses. The compound CF 3CHCl2, for example, is used as a component of refrigerants and blowing agents. It can also be converted by photooxidation into trifluoroacetyl chloride.
- It is already known that compounds, which contain the molecular group CF 2Cl—CF, can be iomerized into compounds which contain the CF3—CCl group. Usually, aluminum trichloride is used as an isomerization catalyst. The aim of this conversion may, for example, be the synthesis of an asymmetric compound from a symmetric compound. For example, HCFC-123 can be synthesized by isomerizing HCFC-123a over aluminum chloride. Such an isomerization may also be carried out for the purpose of purifying HCFC-123, which is contaminated, for example, by HCFC-123a.
- It is an object of the invention to provide an improved method for preparing compounds which contain a CF 3 group.
- Another object of the invention is to provide a new method for the preparation of compounds which contain the CF 3 group, in which the method is carried out via an isomerization reaction.
- An additional object of the invention is to provide a method for purifying compounds which contain the CF 3 group which are contaminated by isomeric contaminants.
- These and other objects have been achieved in accordance with the present invention by providing a method for preparing a compound corresponding to the formula CF 3—CClXY (I) in which X represents H, Cl or F, and Y represents H, Cl, F, C1-C3 alkyl, or C1-C3 alkyl substituted by at least one halogen atom, with the proviso that X and Y cannot simultaneously represent fluorine, the method comprising contacting at least one compound selected from the group consisting of compounds corresponding to the formula CF2Cl—CFXY (II) and compounds corresponding to the formula CFCl2—CF2Y (III), in which X and Y have the meanings given above, with an antimony compound corresponding to the formula SbCl0-0.5 F4.5-5.
- In accordance with the method of the invention for preparing compounds of the formula (I)
- CF3—CClXY (I)
- in which X represents H, Cl or F and Y represents H, Cl, F, C1-C3 alkyl, or C1-C3 alkyl substituted by at least one halogen atom, with the proviso that X and Y cannot simultaneously represent fluorine,
- compounds of the formula (II)
- CF2Cl—CFXY (II)
- or compounds of the formula (III)
- CFCl2—CF2Y (III),
- in which X and Y have the meanings given above, are contacted with the antimony compound SbCl 0-0.5F4.5-5. Advantageously, HF is also present at the same time. If, in this case, the sum of the HF and the antimony compound in the reaction mixture is 100 parts by weight, the HF is contained in an amount of 1 to 70 parts by weight and preferably of 20 to 50 parts by weight, the remainder up to 100 parts by weight being the antimony compound. If, in accordance with a preferred embodiment, HF is present, it may be assumed that the antimony compounds will be present in the form of HF adducts. In this case, contacting is carried out in the presence of HF adducts of SbCl0-0.5F4-4.5. A portion of not more than 10 mole percent of the antimony compound can also be replaced by Sb(III), for example, by SbF3.
- Preferably, the contacting is carried out with antimony pentafluoride (in this connection, it should be kept in mind that, in the presence of HF, adducts of the antimony(V) compound are present, as mentioned above). Antimony pentafluoride is a commercially available product. The highly fluorinated SbCl 0-0.5F4.5 can also be prepared from SbCl5 or SbCl3 and chlorine, as well as sufficient HF and SbF5 as described in Schulz et al., U.S. Pat. No. 6,645,451 (=EP 816,287).
- The isomerization is carried out at a temperature ranging from 20° to 150° C., and preferably from 50° to 120° C. The pressure depends on the composition of the mixture and advantageously ranges from atmospheric pressure to 6 bar. The temperature and pressure are selected, in particular, so that the contacting is carried out in the liquid phase.
- The molar ratio of the compound of formula (II), the compound of formula (III), or the sum of the two compounds when both are present, to the antimony compound preferably ranges from 0.1:1 to 10:1, and particularly preferably from 0.5:1 to 2:1.
- Advantageously, the isomerization is carried out in a corrosion-resistant apparatus. Reactors and equipment parts which consist of aluminum or polytetrafluoroethylene (Teflon™) or are coated with aluminum or polytetrafluoroethylene (Teflon™) have proven to be particularly corrosion-resistant. In the case reactors made of metallic materials, a pre-fluorination with HF or F 2 carried out before the start of the reaction has been shown to have a positive effect on the corrosion behavior. Equipment made from alloys such as those described in Braun et al., WO 03/054241 (=DE 101 63 171) is very suitable. These alloys contain at least 3.5% by weight of aluminum, as well as nickel and/or silicon. Alloys are preferred which consist of or contain 80 to 92% by weight of aluminum and 8 to 20% by weight of silicon or which contain or consist of 3.5 to 10% by weight of aluminum and 90 to 96.5% by weight of nickel.
- The method of the invention can be carried out batchwise or continuously. The reaction can be conducted continuously in a bubble reactor, whereby the educt, or if HF is used at the same time, a mixture of HF and educt, is passed into the liquid antimony compound, and a mixture of product and HF is discharged. In the case of HCFC-123, the product mixture is an azeotrope with HF, which, upon cooling, separates in the liquid phase into two phases.
- It is well known that Sb(V) halide decomposes with formation of Sb(III) halide and halogen. If desired, Sb (II) halide can be converted once again into Sb(V) halide with chlorine or fluorine. This can be done batchwise or continuously, for example, with constant removal of a portion of the reaction mixture and treatment of the latter with halogen.
- The invention thus provides a novel method of effecting isomerization. The palette of usable isomerization catalysts is accordingly expanded.
- The following example is intended to illustrate and explain the invention in further detail without limiting its scope.
- Synthesis of Isomerically Pure 1,1,1-trifluoro-2,2-dichloroethane (123) by Catalytic Isomerization of 1,1,2-trifluoro-1,2-dichloroethane (123a) and 1,2,2-trifluoro-1,1-dicholoroethane (123b) Contained Therein, with Fluorinated Sb Catalysts.
Formulation: Molecular Material Weight Weight in g Moles 123 153.00 38.25 0.25 SbF5 216.75 11.88 0.05 HF 20.00 9.37 0.47 - Procedure:
- A mixture of 89.9% of 123, 10.0% of 123a and 0.1% of 123b was added to an autoclave with a Teflon™ liner and mixed in a ratio of 1:2 with the catalyst mixture. The composition of the catalyst was as follows:
- 55.47% by weight of SbF 5
- 0.64% by weight of SbF 3
- 43.82% HF
- 0.07% by weight of HCl
- The autoclave was closed, heated to 110° C. and maintained at this temperature for one hour at a pressure of about five bar. It is assumed that an HF adduct of antimony pantafluoride was present in the reactor. Subsequently the autoclave was cooled with ice, and the pressure in the gas phase was relieved. The contents of the autoclave were hydrolyzed in ice/tartaric acid (tartaric acid because of the solubility of the Sb complex) (closed system) and the organic phase was separated from the aqueous phase. The purity of the 123 isomer isolated was 99.9%; in addition, 0.14% of newly formed 1,1,2-trifluoro-1,2,2-trichloroethane (113) were present. An additional Sb′″ content of 1% was detected by the analysis of the aqueous phase treated with tartaric acid.
- The foregoing description and examples have been set forth merely to illustrate the invention and are not intended to be limiting. Since modifications of the described embodiments incorporating the spirit and substance of the invention may occur to persons skilled in the art, the invention should be construed broadly to include all variations within the scope of the appended claims and equivalents thereof.
Claims (18)
1. A method for preparing a compound corresponding to formula (I)
CF3—CClXY (I)
wherein
X represents H, Cl or F, and
Y represents H, Cl, F, C1-C3 alkyl, or C1-C3 alkyl substituted by at least one halogen atom,
with the proviso that X and Y cannot simultaneously represent fluorine,
said method comprising contacting at least one compound selected from the group consisting of compounds corresponding to formula (II)
CF2Cl—CFXY (II)
and compounds corresponding to formula (III)
CFCl2—CF2Y (III),
in which X and Y have the meanings given above,
with an antimony compound corresponding to the formula SbCl0-0.5 F4.5-5.
2. A method according to claim 1 , wherein X and Y each represent Cl.
3. A method according to claim 1 , wherein X represents H, and Y represents Cl.
4. A method according to claim 1 , wherein said method is carried out at a temperature ranging from 20° to 150° C.
5. A method according to claim 4 , wherein said method is carried out at a temperature ranging from 50° to 120° C.
6. A method according to claim 1 , wherein the molar ratio of the compound of formula (II) or the compound of formula (III) or of the sum of the compounds of formula (II) and formula (III), to the antimony compound lies in the range from 0.1:1 to 10:1.
7. A method according to claim 6 , wherein the molar ratio lies in the range from 0.5:1 to 2:1.
8. A method of purifying a compound corresponding to formula (I)
CF3—CClXY (I)
contaminated with at least one compound selected from the group consisting of compounds of formula (II)
CF2Cl—CFXY (II)
and compounds of formula (III)
CFCl2—CF2Y (III),
said method comprising treating the contaminated compound of formula (I) according to the method of claim 1 .
9. A method according to claim 8 , wherein the contaminated compound of formula (I) comprises 1,1,1-trifluoro-2,2-dichloroethane contaminated with one or both of 1,1,2-trifluoro-1,2-dichloroethane and 1,2,2-trifluoro-1,1-dichloroethane.
10. A method according to claim 1 , wherein said method is carried out in a corrosion-resistant apparatus.
11. A method according to claim 10 , wherein the apparatus is coated with or made of aluminum.
12. A method according to claim 10 , wherein the apparatus is coated with or made of polytetrafluoroethylene.
13. A method according to claim 1 , wherein the contacting is carried out in liquid phase.
14. A method according to claim 1 , wherein said method is carried out batchwise.
15. A method according to claim 1 , wherein said method is carried out continuously.
16. A method according to claim 1 , wherein said method is carried out in a reaction mixture containing 1 to 70 parts by weight of HF and 30 by 99 parts by weight of antimony compound, whereby the sum of the HF and the antimony compound amounts to 100 parts by weight.
17. A method according to claim 1 , wherein said method is carried out in a reactor having an inner surface which is at least partially fluorinated.
18. A method according to claim 1 , wherein said method is carried out in the presence of HF and the antimony compound is present in form of an HF adduct.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10143177.5 | 2001-09-04 | ||
| DE10143177A DE10143177A1 (en) | 2001-09-04 | 2001-09-04 | Making connections with the CF3 group |
| PCT/EP2002/009547 WO2003020675A1 (en) | 2001-09-04 | 2002-08-27 | Production of compounds comprising the group cf¿3? |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2002/009547 Continuation WO2003020675A1 (en) | 2001-09-04 | 2002-08-27 | Production of compounds comprising the group cf¿3? |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20040171896A1 true US20040171896A1 (en) | 2004-09-02 |
Family
ID=7697581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/790,686 Abandoned US20040171896A1 (en) | 2001-09-04 | 2004-03-03 | Preparation of compounds with the CF3 group |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20040171896A1 (en) |
| EP (1) | EP1427687A1 (en) |
| JP (1) | JP2005501896A (en) |
| CA (1) | CA2462410A1 (en) |
| DE (1) | DE10143177A1 (en) |
| WO (1) | WO2003020675A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016079122A1 (en) | 2014-11-17 | 2016-05-26 | Solvay Sa | A method for producing a chemical compound and apparatus therefor |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009148191A1 (en) * | 2008-06-05 | 2009-12-10 | Daikin Industries, Ltd. | Process for producing fluorine-containing compound by rearrangement reaction |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3490764A (en) * | 1966-07-16 | 1970-01-20 | Carl K B Mueller | Process and device for depositing leaf or sheet material,especially veneer sheets |
| US4851595A (en) * | 1987-07-07 | 1989-07-25 | E. I. Du Pont De Nemours And Company | Liquid phase halogen exchange process for the manufacture of 1,1,1,2-tetrafluoroethane |
| US5608127A (en) * | 1990-02-09 | 1997-03-04 | E. I. Dupont De Nemours And Company | Halogen exchange process for manufacture of hydrochlorofluoropropanes |
| US6645451B1 (en) * | 1996-06-26 | 2003-11-11 | Solvay Fluor Und Derivate Gmbh | Method of preparing inorganic pentafluorides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0788326B2 (en) * | 1987-11-26 | 1995-09-27 | 旭硝子株式会社 | Method for producing 1,1-dichloro-1,2,2,2-tetrafluoroethane |
| US5055624A (en) * | 1989-03-08 | 1991-10-08 | Atochem | Synthesis of 1,1-dichloro-1,2,2,2-tetrafluoroethane |
-
2001
- 2001-09-04 DE DE10143177A patent/DE10143177A1/en not_active Withdrawn
-
2002
- 2002-08-27 EP EP02797548A patent/EP1427687A1/en not_active Withdrawn
- 2002-08-27 WO PCT/EP2002/009547 patent/WO2003020675A1/en not_active Application Discontinuation
- 2002-08-27 JP JP2003524948A patent/JP2005501896A/en not_active Withdrawn
- 2002-08-27 CA CA002462410A patent/CA2462410A1/en not_active Abandoned
-
2004
- 2004-03-03 US US10/790,686 patent/US20040171896A1/en not_active Abandoned
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3490764A (en) * | 1966-07-16 | 1970-01-20 | Carl K B Mueller | Process and device for depositing leaf or sheet material,especially veneer sheets |
| US4851595A (en) * | 1987-07-07 | 1989-07-25 | E. I. Du Pont De Nemours And Company | Liquid phase halogen exchange process for the manufacture of 1,1,1,2-tetrafluoroethane |
| US5608127A (en) * | 1990-02-09 | 1997-03-04 | E. I. Dupont De Nemours And Company | Halogen exchange process for manufacture of hydrochlorofluoropropanes |
| US6645451B1 (en) * | 1996-06-26 | 2003-11-11 | Solvay Fluor Und Derivate Gmbh | Method of preparing inorganic pentafluorides |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016079122A1 (en) | 2014-11-17 | 2016-05-26 | Solvay Sa | A method for producing a chemical compound and apparatus therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| DE10143177A1 (en) | 2003-03-20 |
| CA2462410A1 (en) | 2003-03-13 |
| WO2003020675A1 (en) | 2003-03-13 |
| JP2005501896A (en) | 2005-01-20 |
| EP1427687A1 (en) | 2004-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: SOLVAY FLUOR UND DERIVATE GMBH, GERMANY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:BRAUN, MAX;BROSCH, CARSTEN;REEL/FRAME:015040/0632 Effective date: 20040303 |
|
| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |